Address Book/Contacts syncing - no go - 10.5.3

Hey guys - something that has happened over the last month. Maybe it is associated with 10.5.3, maybe not. What I do know is that I cannot synch my Address Book to .MAC or the iPhone. Neither will update in either direction.
I noticed the synch first after my first synching with .MAC or at least I think. When I bought my MBP, I tried .Mac and sync'd. This was back in Feb 08. When I finally got around to purchasing .Mac in June, I can't be sure if it was working then.
Since then, I wanted to pass my updates from my Address Book to the iPhone. That doesn't work either. I have checked the obvious things, making sure synching was turned in both iTunes, .Mac prefs. I even tried reseting the Sync History in iSync.
With almost anything that I try, I am having no success. What I have noticed in the System Console is that I get an message saying 'AddressBookSync (cleint id: com.apple.AddressBook) error: Exception running AddressBookSync: you can't sync entries that were never registered by your client'. Not sure what this message is telling me but I get it every time either .Mac or iTunes(iPhone) syncs with my Mac.
Has anyone seen this before? Perhaps you have some suggestions that I can try. I haven't installed 10.5.4 yet mainly due to the fact that I didn't want to complicate any issues til I have figured out what is going on.
Thanks in advance.
--Mickey

I have been synching from system preferences. There was an initial problem caused by having email addresses listed under "Other" rather than Home or Work. Dotmac doesnt have accommodation for "Other" email addresses so these weren't being synched. However, when these had been edited to conform with these dotmac limitations, the email addresses still didn't appear after synch.
I think there is some more basic problem here.

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